Chiral S,S-donor ligands in palladium-catalysed allylic alkylation

Tetrahedron Asymmetry

Volumn 12, Issue 10, 2001, Pages 1469-1474

  Jansat, Susanna ^a   Gómez, Montserrat ^a   Muller, Guillermo ^a   Diéguez, Montserrat ^b   Aghmiz, Ali ^b   Claver, Carmen ^b   Masdeu Bultó, Anna M ^b   Flores Santos, Leticia ^c   Martin, Erika ^c   Maestro, Miguel Angel ^d   Mahía, José ^d  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^d UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001001589     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(01)00260-9     Document Type: Article

References (39)

1. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
2. Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, 1999; Vol. 2, Chapter 24, pp. 833-884.
3. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345 and references cited therein.
4. Gómez, M.; Jansat, S.; Muller, G.; Panyella, D.; van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Goubitz, K.; Fraanje, J. Organometallics 1999, 18, 4970-4981.
5. Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 2015-2018.
6. Williams, J. M. J. Synlett 1996, 705-710 and references cited therein.
7. Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346.
8. Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262.
9. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321.
10. Barbaro, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P. S.; Salzmann, R. Organometallics 1996, 15, 1879-1888.
11. Hiroi, K.; Suzuki, Y.; Kaneko, Y.; Kato, F.; Abe, I.; Kawagishi, R. Polyhedron 2000, 19, 525-528.
12. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905-7920.
13. Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
14. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345.
15. Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364 and references cited therein.
16. Lee, S.-G.; Lim, C. W.; Song, C. E.; Kim, K. M.; Jun, C. H. J. Org. Chem. 1999, 64, 4445-4451.
17. Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247-6251.
18. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
19. Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649-1651.
20. Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046.
21. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
22. Enders, D.; Peters, R.; Lochtman, R.; Raabe, G.; Runsink, J.; Bats, J. W. Eur. J. Org. Chem. 2000, 3399-3426.
23. Diéguez, M.; Orejón, A.; Masdeu-Bultó, A. M.; Echarri, R.; Castillón, S.; Claver, C.; Ruiz, A. J. Chem. Soc., Dalton Trans. 1997, 4611-4618.
24. Diéguez, M.; Ruiz, A.; Claver, C.; Pereira, M. M.; d'A. Rocha Gonsalves, A. M. J. Chem. Soc., Dalton Trans. 1998, 3517-3522.
25. Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Chem. Soc., Dalton Trans. 1999, 3439-3444.
26. Bayón, J. C.; Claver, C.; Masdeu-Bultó, A. M. Coord. Chem. Rev. 1999, 193, 73-145.
27. Flores-Santos, L.; Diéguez, M.; Claver, C.; Masdeu-Bultó, A. M.; Martin, E., to be published elsewhere.
28. 2] with la: Diéguez, M.; Ruiz, A.; Masdeu-Bultó, A. M.; Claver, C. J. Chem. Soc., Dalton Trans. 2000, 4154-4159.
29. Synthesis based on the method described in: von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265-284.
30. Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046-2054.
31. Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
32. The isomers come from the different possibilities: exo/ endo, depending on the relative position of the allyl group and backbone ligand; syn/anti, depending on the sulphur absolute configuration; and/or, syn/anti, depending on the relative position of allylic phenyl group.
33. Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1990, 28, 342-345.
34. V. 4.210, Bruker Analytical X-ray Systems, Madison, WI, 1995.
35. V. 4.050, Bruker Analytical X-ray Systems, Madison, WI, 1995.
36. Program for absorption corrections using Bruker CCD based on the method of Robert Blessing: Blessing, R. H. Acta Crystallogr. 1995, A51, 33.
37. Sheldrick, G. M. SHELXS-97, A Computer Program for Crystal Structure Determination;, University of Göttingen: Germany, 1997.
38. Sheldrick, G. M. SHELXL-91, A Computer Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.
39. PC version, Bruker Analytical X-ray Systems, Madison, WI, 1995.